HCID 22254264, compound → 1-(3-chlorophenyl)piperazin-2-one

HRID 1611611Notes

Reaction equation

C(OC([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([Cl:20])[CH:15]=2)[C:10](=[O:21])[CH2:9]1)=O)(C)(C)C>CCOC(C)=O>[Cl:20][C:16]1[CH:15]=[C:14]([N:11]2[CH2:12][CH2:13][NH:8][CH2:9][C:10]2=[O:21])[CH:19]=[CH:18][CH:17]=1

Participants

Conditions

Temperature: 0 °C

Procedure

Through a solution of Boc-protected piperazinone from Step D (17.19 g, 55.4 mmol) in 500 mL of EtOAc at −78° C. was bubbled anhydrous HC1 gas. The saturated solution was warmed to 0° C., and stirred for 12 hours. Nitrogen gas was bubbled through the reaction to remove excess HC1, and the mixture was warmed to room temperature. The solution was concentrated in vacuo to provide the hydrochloride as a white powder. This material was taken up in 300 mL of CH2Cl2 and treated with dilute aqueous NaHCO3 solution. The aqueous phase was extracted with CH2Cl2 (8×300 mL) until tlc analysis indicated complete extraction. The combined organic mixture was dried (Na2SO4), filtered, and concentrated in vacuo to provide the titled free amine as a pale brown oil.

Workup

customNitrogen gas was bubbled through the reaction
customto remove excess HC1
temperaturethe mixture was warmed to room temperature
concentrationThe solution was concentrated in vacuo

Sources & evidence

ORD record: ord-10d6ae1b9ab145a68e596bdf39437c72
Source dataset: uspto-grants-2006_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06989383B1

Reaction notes

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